Isobutyryl chloride → HCID 11411101, compound

HRID 2286319Notes

Reaction equation

HRID 2286319 reaction equation
[CH3:1][CH:2]1[CH:27]2[O:28][C:26]2([CH3:29])[CH:25]([OH:30])[CH2:24][C:22](=[O:23])[N:21]([CH3:31])[C:14]2=[C:15]([Cl:20])[C:16]([O:18][CH3:19])=[CH:17][C:12](=[CH:13]2)[CH2:11][C:10]([CH3:32])=[CH:9][CH:8]=[CH:7][CH:6]([O:33][CH3:34])[C:5]2([OH:39])[NH:35][C:36]([O:38][CH:3]1[CH2:4]2)=[O:37].[C:40](Cl)(=[O:44])[CH:41]([CH3:43])[CH3:42]>C(N(CC)CC)C.CN(C)C=O>[CH3:1][C@H:2]1[C@H:27]2[O:28][C@@:26]2([CH3:29])[C@@H:25]([O:30][C:40]([CH:41]([CH3:43])[CH3:42])=[O:44])[CH2:24][C:22](=[O:23])[N:21]([CH3:31])[C:14]2=[C:15]([Cl:20])[C:16]([O:18][CH3:19])=[CH:17][C:12](=[CH:13]2)[CH2:11][C:10]([CH3:32])=[CH:9][CH:8]=[CH:7][C@@H:6]([O:33][CH3:34])[C@:5]2([OH:39])[NH:35][C:36]([O:38][C@H:3]1[CH2:4]2)=[O:37]

Participants

5

Reactant 2

HCID 62325Isobutyryl chlorideHCID 5358230HCID 5358230, compound

Product 1

HCID 11411101HCID 11411101, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

In a mixture of 1 ml triethylamine and 50 ml of dimethylformamide was dissolved 100 mg of maytansinol and, while the solution was stirred under ice-cooling, 50 μl of isobutyryl chloride was added dropwise. The mixture was stirred under ice-cooling for 30 minutes and then, at room temperature for 2.5 hours, after which it was distilled under reduced pressure. The residue was dissolved in 10 ml of dichloromethane, washed with water and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was chromatographed and recrystallized as in Reference Example 1. By the above procedure there was obtained 19.4 mg of Ansamitocin P-3.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under ice-
  3. temperaturecooling for 30 minutes
  4. distillationafter which it was distilled under reduced pressure
  5. dissolutionThe residue was dissolved in 10 ml of dichloromethane
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was chromatographed
  10. customrecrystallized as in Reference Example 1

Sources & evidence

ORD record
ord-08fec8384f1b44fa9ceab019bf2f0714
Source dataset
uspto-grants-1981_05
Patent number
US04265814

Reaction notes

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